Family-friendly holiday rentals in Stockbridge

Escape in the Catskills w/hottub

Escape to the Catskills: Your Mountain Retreat No Cleaning Fee! Immerse yourself in the breathtaking beauty of the Catskills. Our cozy retreat offers the perfect blend of relaxation and adventure, whether you're seeking a romantic getaway, a peaceful remote work haven, or an exciting outdoor adventure. Unwind in the hot tub while enjoying stunning world-class panoramic views. Conveniently located near charming towns with unique shops, delectable dining options, and hidden antique treasures.

Everything on one floor 2 Bdrm/1.5 Bth & Pets Ok

All size Dogs & Cats Welcome *Outside backyard is large and surrounded by trees with Firepit, Hammock & Volleyball Net +Watercraft available - Kayaks/Rowboat Swim Platform Indoor Wood Burning Fireplace Fully stocked kitchen and toiletries 10-15 minutes to Bash Bish Falls/Catamount Aerial Park/Ski/Snowboard/Tubing 25-30 minutes to Berkshires Shoe shoeing +November-April: watercraft not available, also weather dependent *Only one neighbor, is to the left, separated by trees and bushes

Waterfront 3BR Home in Hudson Valley, Catskills

Key Residence Features at a glance; Waterfront on the Esopus Creek, Seasonal Kayaks, Rowboat, Dock (approx. Memorial Day weekend-mid October) large yard. Fully equipped kitchen, cable, wireless internet, washer and dryer. Enclosed porch, deck and patio with propane grill and patio furniture. Paved flat driveway, ramp allowing access to first floor, oversize door to first floor bathroom. Three spacious bedrooms with air conditioners. Convenient location close to thruway exits. No boat launch.

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

"238 Main" has two rentals. Only one rental is rented at a time. Rental #1 has 2 bedrooms, FULLY EQUIPPED KITCHEN and is SUPERCLEAN! (SEE THE 1 BEDROOM LISTING #2!) We are conveniently located between Butternut and Catamount ski stations. Fully renovated, large garden, private entrance, terrace and parking space. Queen size beds. High Speed WiFi. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit!

A Victorian "Lady"

Enjoy an old-fashioned vacation right across the street from the Hudson river. Watch the tides, boats, and barges pass by. Dining, kayaking within walking. Historic Hudson, Olana just 10 min. drive. This is a house to relax, use as a base for other activities. It is not intended as a place to party.. It is a quiet neighborhood. I expect my guests to respect that. There is a weekend special. If you book friday/saturday or saturday/sunday the price is $350.00 for the 2 nights. Thanks

Secluded Mountain Getaway with Swimming Pond.

This is the perfect country getaway in a serene wooded setting yet close to town. Great for couples, solo adventurers, and families (with kids). A large deck and yard provide great views of the outdoors. This house is privately set but only a short walk to an inviting shared swim pond, meadow & trails. Area attractions include great hiking, skiing, restaurants, breweries, stores and markets. Near Great Barrington & Hudson and all the Berkshires and Hudson Valley have to offer.

Serenity Retreat: Mountains, Waterfalls, Comfort

Enjoy a tranquil retreat overlooking a peaceful creek, set against gorgeous mountain views and nearby spectacular waterfalls. Just a short drive from Woodstock and Saugerties, NY this home on a serene country lane is a gateway to nature's beauty. With close proximity to local attractions, a lush garden, stunning mountain vistas, and a family-and-pet-friendly yard featuring a fire pit and bad mitten, it's the perfect blend of comfort and adventure.

Saugerties Village Retreat

Charming Village home located 5 minutes from Hits. Walking distance to village restaurants & shopping. Front porch, Private backyard with deck and patio. Large eat in kitchen with separate dining room. Spacious Living room with 2 couches and daybed. Cable TV & Wifi Driveway & street parking for up to 3 cars. washer, dryer, dishwasher . Fully fenced in yard for up to 2 dogs with pre approval from host.

Beautiful cottage at the foot of the Birkshires

Come stay with us in our beautiful cozy cottage, on a small lot located in the heart of Copake Falls, walking distance to Taconic State Park. Enjoy great farm to table dining, ski the Berkshires (just under 10 minutes to Catamount Resort), hike to Bash Bish Falls, bike the Harlem Valley Rail Trail, and swim in the spring fed iron ore pit during the open season.